Asymmetric synthesis and receptor activity of chiral simplified resiniferatoxin (sRTX) analogues as transient receptor potential vanilloid 1 (TRPV1) ligands

被引：9
作者：
Kim, Myeong Seop [1 ]
Ki, Yooran [1 ]
Ahn, Song Yeon [1 ]
Yoon, Suyoung [1 ]
Kim, Sung-Eun [1 ]
Park, Hyeung-Geun [1 ]
Sun, Wei [2 ]
Son, Karam [3 ,4 ]
Cui, Minghua [3 ,4 ]
Choi, Sun [3 ,4 ]
Pearce, Larry V. [5 ]
Esch, Timothy E. [5 ]
DeAndrea-Lazarus, Ian A. [5 ]
Blumberg, Peter M. [5 ]
Lee, Jeewoo [1 ]
机构：
[1] Seoul Natl Univ, Coll Pharm, Pharmaceut Sci Res Inst, Seoul 151742, South Korea
[2] Shenyang Pharmaceut Univ, Shenyang 110016, Liaoning, Peoples R China
[3] Ewha Womans Univ, Grad Sch Pharmaceut Sci, Coll Pharm, Natl Leading Res Lab Mol Modeling & Drug Design, Seoul 120750, South Korea
[4] Ewha Womans Univ, Global Top Res Program 5, Seoul 120750, South Korea
[5] NCI, Lab Canc Biol & Genet, Ctr Canc Res, NIH, Bethesda, MD 20892 USA
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2014年 / 24卷 / 01期
基金：
新加坡国家研究基金会; 美国国家卫生研究院;
关键词：
Vanilloid receptor 1; TRPV1; antagonist; Capsaicin; Resiniferatoxin; Molecular modeling; CAPSAICIN RECEPTORS; ANTAGONISTS; DERIVATIVES;
D O I：
10.1016/j.bmcl.2013.10.064
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
The chiral isomers of the two potent simplified RTX-based vanilloids, compounds 2 and 3, were synthesized employing highly enantioselective PTC alkylation and evaluated as hTRPV1 ligands. The analysis indicated that the R-isomer was the eutomer in binding affinity and functional activity. The agonism of compound 2R was comparable to that of RTX. Docking analysis of the chiral isomers of 3 suggested the basis for its stereospecific activity and the binding mode of 3R. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码：382 / 385
页数：4
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